Silver(I)-Catalyzed Oxidative Cyclopropanation of 1,6-Enynes: Synthesis of 3-Aza-bicyclo[3.1.0]hexane Derivatives

Xia Chen; Zengwei Luo; Yong Chen; Yonghui Zhang

doi:10.1021/acs.orglett.2c03619

Silver(I)-Catalyzed Oxidative Cyclopropanation of 1,6-Enynes: Synthesis of 3-Aza-bicyclo[3.1.0]hexane Derivatives

Org Lett. 2022 Dec 23;24(50):9200-9204. doi: 10.1021/acs.orglett.2c03619. Epub 2022 Dec 9.

Authors

Xia Chen¹, Zengwei Luo², Yong Chen¹, Yonghui Zhang²

Affiliations

¹ State Key Laboratory of Biocatalysis and Enzyme Engineering, National & Local Joint Engineering Research Center of High-throughput Drug Screening Technology, Hubei Key Laboratory of Biotechnology of Chinese Traditional Medicine, School of Life Sciences, Hubei University, Wuhan, Hubei 430062, China.
² Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan, Hubei 430030, China.

PMID: 36484531
DOI: 10.1021/acs.orglett.2c03619

Abstract

A simple Ag(I)-catalyzed oxidative cyclopropanation of heteroatom-tethered 1,6-enynes for the establishment of valuable functionalized 3-aza-bicyclo[3.1.0]hexane is presented, which allows the formation of multiple chemical bonds in one step under 20 mol % silver(I) catalysts and air conditions. This approach is highly atom economical, easy to perform, and free of external oxidants and features good to excellent yields and gram-scale synthesis. The preliminary study showed that an uncommon silver carbenoid intermediate might be involved in this process.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Catalysis
Hexanes* / chemistry
Oxidative Stress
Silver*

Substances

Silver
n-hexane
Hexanes